CN113548980A - Method for preparing cyclododecanone oxime - Google Patents
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- C—CHEMISTRY; METALLURGY
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- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
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Abstract
The invention discloses a method for preparing cyclododecanone oxime. The method comprises the following steps: 1) heating a mixture of cyclododecanone, a solvent, a catalyst, a hydroxylamine protective agent and an auxiliary agent to a set temperature; 2) adding ammonia water and hydrogen peroxide into the mixture obtained in the step 1) for reaction, and after the addition is finished, continuing aging until the reaction is finished. Metal organic framework compounds (MOFs) are used as hydroxylamine protective agents, so that the utilization rate of hydrogen peroxide is improved; the amine oxide or ammonium carboxylate is used as an auxiliary agent, so that the ammoximation reaction rate is improved, and the thermal decomposition rate of hydrogen peroxide is reduced. By adopting the method, the reaction lasts for 1 hour, the conversion rate of the cyclododecanone can reach more than 99.5 percent, and the utilization rate of the hydrogen peroxide can be improved to more than 90 percent.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a method for preparing cyclododecanone oxime.
Background
In the early 80 s of the last century, Enichem company of Italy developed a novel catalytic material, titanium silicalite molecular sieve TS-1, and under the catalytic action of TS-1, cycloalkanone, ammonia and hydrogen peroxide can be subjected to ammoximation reaction to directly prepare cycloalkanone oxime in one step, thereby creating conditions for the production technology of new cycloalkanone oxime. In 1994, Enichem company used ammoximation technology to build 12kt/a caprolactam industrial experimental facility in Porto maragrera, italy, and then ammoximation technology was also used to build caprolactam facilities of more than 10 ten thousand tons, and the development of cyclohexanone ammoximation technology was already mature.
Compared with cyclohexanone ammoximation, the cyclododecanone has large molecular scale, can not enter molecular sieves such as TS-1 and the like, and has low reaction catalytic activity; cyclododecanone itself has poor water solubility and a low reaction rate with hydroxylamine, and thus cyclododecanone ammoximation has much lower reactivity than cyclohexanone.
CN1367166A reports that the main side reaction of Cyclododecanone (CDON) ammoximation to prepare cyclododecanone oxime (CDOX) is as follows:
1)NH3+H2O2→NH2OH+H2O
2)NH2OH+CDON→CDOX+H2O
3)2NH2OH+H2O2→N2+4H2O
4)2H2O2→2H2O+O2
due to the poor reaction activity of cyclododecanone ammoximation, hydroxylamine generated by ammonia and hydrogen peroxide under the catalysis of the titanium-silicon molecular sieve is further oxidized and decomposed by hydrogen peroxide, and in addition, the hydrogen peroxide is also decomposed in the reaction process. Even though the document and CN1421432A report that ammonium salt is used as an auxiliary agent, the utilization rate of hydrogen peroxide is still lower than 90%, and the reaction time required for reaching the cyclododecanone conversion rate of 99.5% is still more than 1 h.
Disclosure of Invention
The invention relates to a method for preparing cyclododecanone oxime. The method can reduce the self thermal decomposition rate of the hydrogen peroxide, improve the utilization rate of the hydrogen peroxide and improve the reaction rate of the ammoximation.
In order to achieve the technical effects, the invention adopts the following technical scheme:
a process for preparing cyclododecanone oxime comprising the steps of:
1) heating a mixture of cyclododecanone, a solvent, a catalyst, a hydroxylamine protective agent and an auxiliary agent to a set temperature;
2) adding ammonia water and hydrogen peroxide into the mixture obtained in the step 1) for reaction, and after the addition is finished, continuing aging until the reaction is finished.
The solvent of the present invention can be selected from but not limited to one or more of methylcyclohexane, ethylcyclohexane, isopropylcyclohexane, dimethylcyclohexane, squalane, methanol, ethanol, isopropanol, tert-butanol, pentanediol, hexanediol, preferably isopropanol; the mass ratio of the solvent to the cyclododecanone is 2:1-10:1, preferably 3:1-5: 1.
The catalyst can be selected from but not limited to TS-1, TS-2, Ti-ZSM-48, Ti-FER, TPSO-5, Ti-MOR, Ti-MCM-41, Ti-ITQ-7, Ti-MWW, Ti-UTD-1, Ti-SBA-15, Ti-HMS and Ti-MTS-9, preferably TS-1 and/or Ti-MWW, further preferably TS-1 and Ti-MWW with the mass ratio of 1:1-1:5, preferably 1:1-1:3, and the problems of short service life of TS-1 and high defect degree of regeneration structure of Ti-MWW can be solved by compounding the catalyst and the Ti-MWW.
The dosage of the catalyst is 1-10%, preferably 3-5% of the mass of the cyclododecanone.
The hydroxylamine protective agent is a metal-organic framework compound (MOFs), is selected from one or more of reticular metal-organic framework materials (IRMOFs), zeotype imidazole framework materials (ZIFs), Levaschil framework Materials (MILs) and pore or channel type framework materials (PCNs), is preferably a zeotype imidazole framework material (ZIFs) with better water resistance, and is more preferably ZIF-8 and/or ZIF-67.
The dosage of the hydroxylamine protective agent is 0.1-5%, preferably 1-3% of the mass of cyclododecanone.
The auxiliary agent is an amine oxide type auxiliary agent or an ammonium carboxylate type auxiliary agent, the amine oxide type auxiliary agent can be one or more of aliphatic amine oxide, aromatic amine oxide and heterocyclic amine oxide, and suitable examples include but are not limited to one or more of dodecyl dihydroxyethyl amine oxide, tetradecyl dihydroxyethyl amine oxide, octadecyl amidopropyl amine oxide, cocamidopropyl amine oxide, laurylamidopropyl amine oxide and N-dodecyl morpholine oxide; the ammonium carboxylate type auxiliary agent can be one or more of rose bengal ammonium tricarboxylate, ammonium oxalate, ammonium acetate, ammonium formate, ammonium benzoate, ammonium citrate, ammonium glycyrrhetate, ammonium tartrate and ammonium malate.
In order to improve the reaction rate of the ammoximation, the invention preferably adopts amine oxide as an auxiliary agent, and the hydrophilic group of the amine oxide is N → O, similar to hydroxylamine; the oleophilic group of the amine oxide is long-chain alkane, is similar to cyclododecanone, has similar and compatible effects, and can assist the release of hydroxylamine and quickly transfer to an oil phase while the hydroxylamine is protected by MOFs, thereby achieving the purposes of protecting the hydroxylamine and increasing the ammoximation reaction rate of the cyclododecanone.
Preferably, the auxiliary agent is selected from one or more of dodecyl dihydroxyethyl amine oxide, lauramide propyl amine oxide and N-dodecyl morpholine oxide.
The dosage of the auxiliary agent is 0.5-15%, preferably 3-6% of the mass of cyclododecanone.
In order to solve the problem that hydroxylamine is oxidized by hydrogen peroxide, the invention uses metal organic framework compounds (MOFs) as hydroxylamine protective agents, metals (such as Zn of ZIF-8 and Co of ZIF-67) in the MOFs can be coordinated with N atoms of hydroxylamine, and simultaneously, the hydrophobicity of the metal organic framework compounds is utilized to prevent the hydrogen peroxide from contacting with the hydroxylamine, so that the purpose of protecting the hydroxylamine is achieved, and the utilization rate of the hydrogen peroxide is improved.
The set temperature of step 1) of the present invention is 70 to 100 ℃, preferably 80 to 90 ℃.
The reaction temperature of the step 2) of the present invention is 70 to 100 ℃, preferably 80 to 90 ℃.
The concentration of the ammonia water of the invention is 10-50 wt%, preferably 20-30 wt%.
The concentration of the hydrogen peroxide is 20-60 wt%, preferably 30-40 wt%.
The feeding time of the ammonia water and the hydrogen peroxide is 10-60min, and preferably 20-30 min.
The molar ratio of the hydrogen peroxide to the cyclododecanone is 1:1-2:1, preferably 1.1:1-1.3: 1.
The molar ratio of ammonia to cyclododecanone in the ammonia water is 1:1-5:1, preferably 2:1-3: 1.
In conclusion, the invention adopts metal organic framework compounds (MOFs) as hydroxylamine protective agents, thereby improving the utilization rate of hydrogen peroxide; the amine oxide or ammonium carboxylate is used as an auxiliary agent, so that the ammoximation reaction rate is improved, and the thermal decomposition rate of hydrogen peroxide is reduced. By adopting the method, the reaction lasts for 1 hour, the conversion rate of the cyclododecanone can reach more than 99.5 percent, and the utilization rate of the hydrogen peroxide can be improved to more than 90 percent.
Detailed Description
The detection method used in the examples is described below:
(1) analysis of reaction conversion
The invention uses gas chromatography area correction normalization analysis to determine the conversion rate and selectivity of cyclododecanone ammoximation reaction, and the chromatographic analysis conditions are as follows:
the instrument model is as follows: shimadzu GC 2010; a chromatographic column: DB-5 (30X 0.32X 0.25); column temperature: temperature programming (60 ℃ for 5min, then heating to 120 ℃ at the heating rate of 6 ℃/min, then heating to 300 ℃ at the heating rate of 20 ℃/min, and keeping for 5 min); sample inlet temperature: 240 ℃; FID temperature: 300 ℃; n is a radical of2Flow rate: 1 mL/min; h2Flow rate: 40 mL/min; shock insulator purging (N)2) Flow rate: 3 mL/min; carrier gas (N)2) Flow rate: 1 mL/min; split-flow sample introduction, split-flow ratio: 50; sample introduction amount: 0.05. mu.L.
(2) Analysis of hydrogen peroxide content
A Swiss Wantong 905 Ai intelligent series full-automatic potentiometric titrator adopts KMnO4Direct titration method.
The main raw material sources are as follows:
metal organic framework compounds ZIF-8 and ZIF-67 from Nanjing pioneer nanomaterial science and technology Limited;
amine oxide surfactants from Suzhou milk chemical Co., Ltd.
TS-1, Ti-MWW, from Nanjing pioneer nanomaterial science and technology, Inc.
Example 1
100g cyclododecanone, 200g isopropanol, 0.5g TS-1, 0.5g Ti-MWW, 0.05g ZIF-8, 0.05g ZIF-67 and 0.5g dodecyldihydroxyethyl amine oxide were added to a 1L stainless steel reaction vessel, stirred and heated to 90 ℃.
And maintaining the reaction temperature, uniformly adding 93g of 30 wt% ammonia water and 68g of 30 wt% hydrogen peroxide into the reaction kettle, feeding for 30min, and continuing aging for 30min after feeding.
After the reaction, the reaction solution was analyzed, and the conversion rate of cyclododecanone was 99.54%, the selectivity of cyclododecanone oxime was 99.2%, and the utilization rate of hydrogen peroxide was 92.3%.
Example 2
100g of cyclododecanone, 1000g of isopropanol, 1.67g of TS-1, 8.33g of Ti-MWW, 3.75g of ZIF-8, 1.25g of ZIF-67 and 15g of lauramidopropyl amine oxide are added into a 1L stainless steel reaction kettle, stirred and heated to 80 ℃.
Maintaining the reaction temperature, uniformly adding 93g of 20 wt% ammonia water and 61g of 40 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 20min, and after the adding is finished, continuing to age for 40 min.
After the reaction, the reaction solution was analyzed, and the conversion rate of cyclododecanone was 99.61%, the selectivity of cyclododecanone oxime was 99.6%, and the utilization rate of hydrogen peroxide was 94.1%.
Example 3
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW, 1.67g of ZIF-8, 0.83g of ZIF-67 and 4g N-dodecyl-morpholine-oxide are added into a 1L stainless steel reaction kettle, stirring is started, and the temperature is raised to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion rate of cyclododecanone was 99.80%, the selectivity of cyclododecanone oxime was 99.7%, and the utilization rate of hydrogen peroxide was 96.7%.
Example 4
100g of cyclododecanone, 1000g of isopropanol, 8.33g of Ti-MWW, 3.75g of ZIF-8 and 15g of lauramidopropylamine oxide are added into a 1L stainless steel reaction kettle, stirred and heated to 80 ℃.
Maintaining the reaction temperature, uniformly adding 93g of 20 wt% ammonia water and 61g of 40 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 20min, and after the adding is finished, continuing to age for 40 min.
After the reaction, the reaction solution was analyzed, and the conversion rate of cyclododecanone was 99.52%, the selectivity of cyclododecanone oxime was 99.1%, and the utilization rate of hydrogen peroxide was 91.4%.
Example 5
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW, 1.67g of ZIF-8, 0.83g of ZIF-67 and 4g of ammonium malonate were added to a 1L stainless steel reaction kettle, stirred and heated to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 99.51%, the selectivity of cyclododecanone oxime was 99.0%, and the utilization rate of hydrogen peroxide was 90.3%.
Comparative example 1
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW and 4g N-dodecyl morpholine oxide are added into a 1L stainless steel reaction kettle, the stirring is started, and the temperature is raised to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 82.10%, the selectivity of cyclododecanone oxime was 97.7%, and the utilization rate of hydrogen peroxide was 79.9%.
Comparative example 2
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW, 2.5g of ferric benzoate and 4g N-dodecyl morpholine oxide are added into a 1L stainless steel reaction kettle, stirred and heated to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 83.51%, the selectivity of cyclododecanone oxime was 97.8%, and the utilization rate of hydrogen peroxide was 81.7%.
Comparative example 3
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW, 1.67g of ZIF-8 and 0.83g of ZIF-67 were added to a 1L stainless steel reaction kettle, stirred and heated to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 79.24%, the selectivity of cyclododecanone oxime was 97.9%, and the utilization rate of hydrogen peroxide was 85.3%.
Comparative example 4
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW, 1.67g of ZIF-8, 0.83g of ZIF-67 and 4g of stearic acid are added into a 1L stainless steel reaction kettle, stirred and heated to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 92.13%, the selectivity of cyclododecanone oxime was 98.4%, and the utilization rate of hydrogen peroxide was 88.4%.
Comparative example 5
100g of cyclododecanone, 400g of isopropanol and 2.67g of Ti-MWW are added into a 1L stainless steel reaction kettle, stirring is started, and the temperature is raised to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion of cyclododecanone was 74.66%, the selectivity of cyclododecanone oxime was 96.9%, and the utilization rate of hydrogen peroxide was 71.4%.
Comparative example 6
100g of cyclododecanone, 400g of isopropanol, 1.33g of TS-1, 2.67g of Ti-MWW and 1.67g of ZnCl2、0.83g CoCl2And 4g N-Dodecyloxygroline into 1L stainless steelIn the reaction kettle, stirring is started, and the temperature is raised to 85 ℃.
And maintaining the reaction temperature, uniformly adding 80g of 27 wt% ammonia water and 66g of 34 wt% hydrogen peroxide into the reaction kettle, wherein the adding time is 24min, and after the adding is finished, continuing to age for 36 min.
After the reaction, the reaction solution was analyzed, and the conversion rate of cyclododecanone was 30.31%, the selectivity of cyclododecanone oxime was 97.2%, and the utilization rate of hydrogen peroxide was 26.7%.
Finally, it should be noted that the above-mentioned embodiments only illustrate the preferred embodiments of the present invention, and do not limit the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that various changes and modifications can be made by modifying the technical solution of the present invention or equivalent substitutions within the scope of the present invention defined by the claims.
Claims (10)
1. A process for preparing cyclododecanone oxime comprising the steps of:
1) heating a mixture of cyclododecanone, a solvent, a catalyst, a hydroxylamine protective agent and an auxiliary agent to a set temperature;
2) adding ammonia water and hydrogen peroxide into the mixture obtained in the step 1) for reaction, and after the addition is finished, continuing aging until the reaction is finished.
2. The process according to claim 1, wherein the catalyst is selected from one or more of TS-1, TS-2, Ti-ZSM-48, Ti-FER, TPSO-5, Ti-MOR, Ti-MCM-41, Ti-ITQ-7, Ti-MWW, Ti-UTD-1, Ti-SBA-15, Ti-HMS, Ti-MTS-9, preferably TS-1 and/or Ti-MWW, further preferably TS-1 and Ti-MWW in a mass ratio of 1:1 to 1:5, preferably 1:1 to 1: 3.
3. The process according to claim 1 or 2, characterized in that the catalyst is used in an amount of 1-10%, preferably 3-5% by mass of cyclododecanone.
4. A method according to any one of claims 1-3, wherein the hydroxylamine protecting agent is a metal-organic framework compound, preferably one or more from the group consisting of a reticulated metal-organic framework material, a zeoligmazole-like framework material, a levator framework material, a pore or channel framework material, more preferably a zeoligmazole-like framework material, further preferably ZIF-8 and/or ZIF-67.
5. A process according to any one of claims 1 to 4, characterized in that the hydroxylamine protecting agent is used in an amount of 0.1 to 5%, preferably 1 to 3% by mass of cyclododecanone.
6. The method according to any one of claims 1 to 5, characterized in that the auxiliary agent is an amine oxide type auxiliary agent and/or an ammonium carboxylate type auxiliary agent, the amine oxide type auxiliary agent being preferably selected from one or more of aliphatic amine oxides, aromatic amine oxides, heterocyclic amine oxides, more preferably one or more of dodecyl dihydroxyethyl amine oxide, tetradecyl dihydroxyethyl amine oxide, octadecyl amidopropyl amine oxide, cocamidopropyl amine oxide, lauramidopropyl amine oxide, N-dodecyl morpholine oxide; the ammonium carboxylate type auxiliary agent is preferably one or more of rose bengal ammonium tricarboxylate, ammonium oxalate, ammonium acetate, ammonium formate, ammonium benzoate, ammonium citrate, ammonium glycyrrhetate, ammonium tartrate and ammonium malate.
7. The method according to any one of claims 1 to 6, wherein the auxiliary agent is selected from one or more of dodecyl dihydroxyethyl amine oxide, lauramidopropyl amine oxide, and N-dodecyl morpholine oxide.
8. A process according to any one of claims 1 to 7, characterised in that the auxiliaries are used in an amount of from 0.5 to 15%, preferably from 3 to 6%, based on the mass of cyclododecanone.
9. The method according to any one of claims 1 to 8, wherein the set temperature of step 1) is 70 to 100 ℃, preferably 80 to 90 ℃.
10. The process according to any one of claims 1 to 9, wherein the reaction temperature of step 2) is 70 to 100 ℃, preferably 80 to 90 ℃; and/or the feeding time of the ammonia water and the hydrogen peroxide is 10-60min, preferably 20-30 min.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736087A (en) * | 2024-02-19 | 2024-03-22 | 天津市科密欧化学试剂有限公司 | Preparation method of triammonium rhodotricarboxylic acid |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1367166A (en) * | 2001-01-26 | 2002-09-04 | 德古萨公司 | Method for preparing oxime by using ammonium salt or substituted ammonium salt through cocatalysis |
| CN102906065A (en) * | 2010-03-24 | 2013-01-30 | 宇部兴产株式会社 | Method for producing oxime |
| CN103864643A (en) * | 2014-03-04 | 2014-06-18 | 华东师范大学 | Preparation method of oxime |
| WO2017210874A1 (en) * | 2016-06-08 | 2017-12-14 | Xia, Ling | Imperfect mofs (imofs) material, preparation and use in catalysis, sorption and separation |
| CN110272356A (en) * | 2019-07-25 | 2019-09-24 | 万华化学集团股份有限公司 | A kind of method of cyclododecanone oximate |
| CN110372536A (en) * | 2019-08-15 | 2019-10-25 | 中触媒新材料股份有限公司 | A kind of method of preparing cyclohexanone oxime by ammoximation of cyclohexanone |
-
2020
- 2020-04-23 CN CN202010324514.8A patent/CN113548980B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1367166A (en) * | 2001-01-26 | 2002-09-04 | 德古萨公司 | Method for preparing oxime by using ammonium salt or substituted ammonium salt through cocatalysis |
| CN102906065A (en) * | 2010-03-24 | 2013-01-30 | 宇部兴产株式会社 | Method for producing oxime |
| CN103864643A (en) * | 2014-03-04 | 2014-06-18 | 华东师范大学 | Preparation method of oxime |
| WO2017210874A1 (en) * | 2016-06-08 | 2017-12-14 | Xia, Ling | Imperfect mofs (imofs) material, preparation and use in catalysis, sorption and separation |
| CN110272356A (en) * | 2019-07-25 | 2019-09-24 | 万华化学集团股份有限公司 | A kind of method of cyclododecanone oximate |
| CN110372536A (en) * | 2019-08-15 | 2019-10-25 | 中触媒新材料股份有限公司 | A kind of method of preparing cyclohexanone oxime by ammoximation of cyclohexanone |
Non-Patent Citations (1)
| Title |
|---|
| 卢福军 等: "钛硅分子筛催化合成酮肟的工艺研究", 应用化工, vol. 45, no. 6, pages 1036 - 1039 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117736087A (en) * | 2024-02-19 | 2024-03-22 | 天津市科密欧化学试剂有限公司 | Preparation method of triammonium rhodotricarboxylic acid |
| CN117736087B (en) * | 2024-02-19 | 2024-05-03 | 天津市科密欧化学试剂有限公司 | Preparation method of triammonium rhodotricarboxylic acid |
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